Novel ring expansion routes are proposed for synthesis of 8,9,13, 14-disecosteroid molecules that are large ring analogs of estrone, progesterone, and other hormones with potential birth control properties. A variation leading to the growth stimulant zearalanone and related systems with part of the zearalanone functionality is also outlined. The key ring expansions utilize acid catalyzed rearrangements, thermal or anionic sigmatropic shifts and benzyne reactions. Experiments are also described which probe the stereochemistry of the thermal and anionic sigmatropic shifts.